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What do you mean by "sideloading"?
My intention, when I bought my 505, was to use it entirely for free ebooks -- as I put it, "so I can read Project Gutenberg in bed." It's wonderful for that. I have ended up buying ebooks for it as well, but not from the Sony store; from Baen, O'Reilly, BVC, and a few other random places. My recommendation to everyone is Sony+calibre. But ... I'm also very much a techie, so I don't know how that will fly with your correspondent.
I've always found it baffling that people who have mastered complex and intricate things such as being able to hold a conversation with another person find it difficult to use a piece of technology that is not only built to be used easily, but comes with instructions!
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